Radical-Type Difunctionalization of Alkenes with CO2

doi:10.6023/A19060208

Acta Chimica Sinica ›› 2019, Vol. 77 ›› Issue (9): 783-793.DOI: 10.6023/A19060208 Previous Articles Next Articles

Special Issue: 有机自由基化学

Perspective

二氧化碳参与的自由基型烯烃双官能团化反应

张振^a^b, 龚莉^b, 周晓渝^b, 颜思顺^b, 李静^b^*(), 余达刚^b^*()

^a成都大学药学与生物工程学院农业农村部杂粮加工重点实验室成都 610106
^b四川大学化学学院绿色化学与技术教育部重点实验室成都 610064

投稿日期:2019-06-12 发布日期:2019-07-12
通讯作者: 李静,余达刚 E-mail:jingli@scu.edu.cn;dgyu@scu.edu.cn
作者简介:张振, 特聘副研究员, 1985年出生于山西怀仁市, 2007年在四川大学化学学院获得学士学位, 2017年在中科院成都有机所获得博士学位(导师: 支永刚研究员和余达刚教授), 随后在成都大学药学与生物工程学院工作至今. 其研究兴趣主要是药物合成、二氧化碳化学.|李静, 助理研究员, 1981年出生于四川广安市, 2006年在四川大学化学学院获得学士学位, 2009年在四川大学化学学院获得硕士学位(导师: 余孝其教授), 随后在四川抗菌素工业研究所工作至2012年, 2012年6月在四川大学化学学院工作至今. 其研究兴趣主要是二氧化碳化学、无机-有机杂化材料的合成.|余达刚, 2007年本科毕业于四川大学化学学院, 2012年博士毕业于北京大学化学与分子工程学院(导师: 施章杰教授), 2012~2014年作为洪堡学者在德国明斯特大学(导师: Frank Glorius教授)开展博士后研究, 2015年回到四川大学开展教学和独立研究工作, 被聘为教授、博士生导师. 主要从事二氧化碳利用和可见光催化等绿色可持续发展化学研究, 已发表学术论文60余篇, 参与攥写英文专著2个章节, 受邀在国内外会议上做邀请报告和主题报告10余次. 曾入选2015年中组部“青年千人”、四川省“青年千人”和2016年“Organic Chemistry Frontiers” Emerging Investigators; 主持了2018年国家自然科学基金委优秀青年基金和霍英东青年教师基金等多项科研项目; 曾获得2017年Thieme Chemistry Journal Award、2017年ACP Lectureship Awards、2018年中国化学会青年化学奖、2018年四川大学“优秀教师”等奖励.
基金资助:
项目受科技部“973”(No.2015CB856600);国家自然科学基金(Nos.21822108);国家自然科学基金(21801025);教育部霍英东基金(No.161013);中央高校基本业务费资助

Radical-Type Difunctionalization of Alkenes with CO₂

Zhang, Zhen^a^b, Gong, Li^b, Zhou, Xiao-Yu^b, Yan, Si-Shun^b, Li, Jing^b^*(), Yu, Da-Gang^b^*()

^aKey Laboratory of Coarse Cereal Processing (Ministry of Agriculture and Rural Affairs), College of Pharmacy and Biological Engineering, Chengdu University, Chengdu 610106
^bKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064

Received:2019-06-12 Published:2019-07-12
Contact: Li, Jing,Yu, Da-Gang E-mail:jingli@scu.edu.cn;dgyu@scu.edu.cn
Supported by:
Project supported by the “973” Project from the Ministry of Science and Technology of China(No.2015CB856600);the National Natural Science Foundation of China(Nos.21822108);the National Natural Science Foundation of China(21801025);the Fok Ying Tung Education Foundation(No.161013);the Fundamental Research Funds for the Central Universities.

CO₂ is an ideal C1 source in chemical transformations. It is of great significance to utilize CO₂ in chemical conversion to synthesize high value-added compounds, including carboxylic acids and carbonyl-containing heterocycles. On the other hand, the difunctionalization of olefins is an important organic reaction, which can efficiently convert easily available olefins into important compounds with structural diversity. However, due to the low reactivity of CO₂ and the difficulty in controlling the selectivity, the difunctionalization of olefins with CO₂ is highly challenging. Recently, the significant progress of radical chemistry has provided new strategies and promoted the development of novel transformations in this field. This Perspective summarizes the recent progress of the radical-type difunctionalization of olefins with CO₂, including the oxy-alkylation, carbocarboxylation, silacarboxylation, thiocarboxylation, and dicarboxylation of alkenes with CO₂. At the same time, we also highlight the mechanism with radicals and four kinds of pathways are proposed: (1) Free radicals attack olefins to form new carbon radical intermediates. The radicals are then oxidized to form carbocations, which are further captured by carbonates or carbamates. It is also possible for direct C—O bonding reaction or sequent C—I and C—O bonds formation. (2) The new carbon radical intermediates, in-situ generated through attack of alkenes with radicals, are reduced via single electron transfer into carbanions, which could attack CO₂to form C—C bonds. (3) CO₂is reduced into CO₂ radical anions in the highly reductive reaction conditions. Once generated, the CO₂ radical anions might attack olefins to form carboxylate bearing more stable carbon radical intermediates (such as benzylic ones) and further form C—C bonds or carbon-heteroatom bonds. (4) Olefins are reduced via single electron transfer into alkenyl free radical anions in the highly reductive reaction conditions. These anions may attack CO₂to form carboxylate bearing carbon radical intermediates and are further reduced to generate carbanions. Finally they may attack another CO₂to form succinic acid derivatives. We point out the challenges and predict the future development in the field, including the more challenging substrates, more reaction types, better selectivities, and deeper mechanistic understanding.

Key words: carbon dioxide, olefin, difunctionalization, radical, visible-light photoredox catalysis

Cite this article

Zhang, Zhen, Gong, Li, Zhou, Xiao-Yu, Yan, Si-Shun, Li, Jing, Yu, Da-Gang. Radical-Type Difunctionalization of Alkenes with CO₂[J]. Acta Chimica Sinica, 2019, 77(9): 783-793.

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Fig. & Tab. 15

Figure 1. Radical-type difunctionalization of alkenes with CO2

Figure 2. Selective oxytrifluoromethylation of allylamines with CO2

Figure 3. Radical trifluoromethylative dearomatization of indoles and furans with CO2

Figure 4. Carboxylative cyclization of allyl amines with CO2

Figure 5. Carboxylative cyclization of allyl alcohols with CO2

Figure 6. Oxy-difluoroalkylation of allylamines with CO2

Figure 7. Oxy-alkylation of allylamines via visible-light-driven palladium catalysis

Figure 8. Dicarbofunctionalization of styrenes with CO2

Figure 9. A proposed mechanism of dicarbofunctionalization of styrenes with CO2 and radical precursors

Figure 10. Dicarbofunctionalization of alkenes with CO2 and silanes or alkanes

Figure 11. A proposed mechanism of dicarbofunctionalization of alkenes with CO2 and silanes or alkanes

Figure 12. Visible-light-driven iron-promoted thiocarboxylation of alkenes with CO2

Figure 13. A proposed mechanism of visible-light-driven iron-promoted thiocarboxylation of alkenes with CO2

Figure 14. Electrosynthesis of 2-phenylsuccinic acids with CO2 by Senboku and Tokuda group

Figure 15. Electrochemical dicarboxylation of arylalkenes and 1,3-dienes with CO2 by Jiang group

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二氧化碳参与的自由基型烯烃双官能团化反应

Radical-Type Difunctionalization of Alkenes with CO₂

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